This is an excerpt from my recently released book that can be purchased here

One of the preeminent historians of our time, Garry Wills, tells us in his 2002 biography of Madison, that on January 3rd, 1811, Madison sent a secret message to Congress asking for $100 ,000 to stir up a rebellion in East Florida to match which was already taking place in West Florida. 

 In early 1812, General George Matthews and Colonel John McKee were commissioned by President Madison as agents with secret instructions to try and acquire East Florida from Spain and bring this territory into the United States. Mathews and McKee also had authorization to either negotiate or take the territory between the Perdido and Suwannee Rivers that were still being governed from Pensacola. 

The Spanish had in fact already placated American interests by repealing the decree that harbored runaway slaves. The Jefferson Administration, never ending in its quest to protect southern interests and the private property rights of southern farmers and plantation owners had urged Spain diplomatically to repeal the decree from the 1680’s. Spain had done so, but given the state of anarchy that characterized both West and East Florida in this period the runaways continued. And despite the earlier failure of the State of Muscogee, Seminole natives continued to harbor runaways. 

Spain was now aligned with Britain, and was fighting the Peninsula War against France on the Iberian Peninsula in alliance with Britain. When Britain won the Battle of Trafalgar in 1805 off the Spanish coast, Spain’s Royal Family had aligned with France. But Napoleon’s 1807 invasion of the Iberian Peninsula changed European affairs in this arena, forcing Spanish loyalists and colonial officials into a shotgun alliance with Britain. 

This is a completely different situation than the past when we’ve discussed in past volumes of this series. Specifically the War of Jenkins Ear, or Queen Anne’s War. Those pitted Britain, holder of the Thirteen Colonies against Spain, holder of Florida. It was also different from the American Revolutionary War where the United States to the north was aligned with Spain against Britain who owned east and west Florida. 

So, significantly for the first time Britain and Spain are aligned with one another while the American colonists, now the United States  are on the other side. This is a reversal of the previous colonial conflicts in Florida.  Meanwhile, unsurprisingly, the natives line up behind the British.

 So strong was the Seminole and Miccosukee commitment to the British side, that some natives based in Florida even made their way to the Chesapeake front of the war in 1814, to fight alongside the British. While records are vague it is a possible one or two were even involved in the burning of Washington D.C.! 

President Madison wanted to secure East Florida just as they were working to secure West Florida or take west Florida by military force before it fell extensively into British hands. 

Madison instructions were murky but Secretary of State James Monroe ordered McKee and Matthews not to seize the territory. The goal was to try and negotiate with the Spanish colonial authorities. 

While Monroe’s instructions were clear, things went in a completely different course. McKee and Matthews were wrong for the job and were more interested in adventure and conquest. This is part of a theme of history in general, where James Madison as president tended to pick the wrong people for big jobs. Besides that, Madison was keenly aware that he was to face a serious challenge for reelection (the only serious challenge any of the founding generation got in a reelection campaign was Madison’s 1812 effort) so he backed off. 

Madison is remembered fondly as a founding father, as a co -author of the Federalist papers, as the father of the constitution. Without a doubt he was one of the most important figures in American History, in a positive sense.  From my vantage point that has skewed the perception of his Presidency. 

I think Madison was a very poor president, who tended to pick the wrong people for jobs and also got many of the big decisions wrong during his Presidency. When compared to his two close friends, James Monroe and Thomas Jefferson, who succeeded and preceded him respectively, he doesn’t stand up as well in terms of his two terms as President. 

Eventually McKee decided to bow out of the mission, but Matthews proceeded. The sole American agent then moved into a house in St. Marys, Georgia, which is right across the St. Marys River and Cumberland Sound from Fernandina Beach, on Amelia Island. The house was ironically just down the street from a safehouse where Aaron Burr had hid out after killing Alexander Hamilton in 1804. Burr then had escaped west and linked up with the aforementioned General James Wilkinson (then a Colonel) to try and woo Spanish authorities into attacking the United States. 

By this time Fernandina Beach and Amelia Island were mostly populated with American settlers. They had been offered incentives to acquire land and start business in Spanish East Florida. 

On June 25, 1812 the US House of Representatives voted to annex all of Florida. 

So things appear straightforward for Matthews. 

But they weren’t quite that simple. In St. Marys, what Matthews found was that there were a lot of people on the Georgia side of the boundary  who felt like Spanish Florida was great, that they were enjoying an economic boom in southern Georgia thanks to the markets that Spain had opened up.

The residents of St Marys were doing business with Fernandina and Amelia Island. The status quo suited them. They were going to prove less helpful to Matthews than originally anticipated.